Pyridine → HCID 303421, compound

HRID 378171Notes

Reaction equation

HRID 378171 reaction equation
[C:1](Cl)(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:12]1([SH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.N1C=CC=CC=1>ClCCl>[C:1]([S:18][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7969ThiophenolHCID 660233-Phenylprop-2-enoyl chloride

Product 1

HCID 303421HCID 303421, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of cinnamoyl chloride (14.6 g, 87.68 mmol) in dichloromethane (100 mL) was added to a solution of thiophenol (9.55 g, 86.68 mmol) and pyridine (7 mL) in dichloromethane (150 mL) in an ice-water bath. After 18 hours at room temperature, the reaction mixture was washed with dilute hydrochloric acid (100 mL, 1N), brine (100 mL), dried (MgSO4) and was concentrated to afford 19.0 g (91%) of the desired thioester as a crystalline solid.

Workup

  1. washthe reaction mixture was washed with dilute hydrochloric acid (100 mL, 1N), brine (100 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationwas concentrated

Sources & evidence

ORD record
ord-63ed0bc2d74f4fafad517b6c55ab88d6
Source dataset
uspto-grants-2000_02
Patent number
US06028223

Reaction notes

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